Citric Acid → N-(4-azido-2-nitrophenyl)-N'-(N-((2-hydroxyethyldithio)-2-ethylamidosuccinimido)-3-aminopropyl)-N'-methyl-1,3-propanediamine citrate salt

HRID 1460044Notes

Reaction equation

HRID 1460044 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][CH2:18][NH:19][N:20]2[C:24](=[O:25])[CH2:23][CH:22]([NH:26][C:27](=[O:34])[CH2:28][S:29][S:30][CH2:31][CH2:32][OH:33])[C:21]2=[O:35])[CH3:15])=[C:6]([N+:36]([O-:38])=[O:37])[CH:5]=1)=[N+:2]=[N-:3].[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42]>CO>[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42].[N:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][CH2:18][NH:19][N:20]2[C:24](=[O:25])[CH2:23][CH:22]([NH:26][C:27](=[O:34])[CH2:28][S:29][S:30][CH2:31][CH2:32][OH:33])[C:21]2=[O:35])[CH3:15])=[C:6]([N+:36]([O-:38])=[O:37])[CH:5]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 86751760N-(4-azido-2-nitrophenyl)-N'-(N-((2-hydroxyethyldithio)-2-ethylamidosuccinimido)-3-aminopropyl)-N'-methyl-1,3-propanediamine

Product 1

HCID 86751761N-(4-azido-2-nitrophenyl)-N'-(N-((2-hydroxyethyldithio)-2-ethylamidosuccinimido)-3-aminopropyl)-N'-methyl-1,3-propanediamine citrate salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The reaction was carried out in the dark. A flask charged with a solution of 1.15 (2.12 mmole) of N-(4-azido-2-nitrophenyl)-N'-(N-((2-hydroxyethyldithio)-2-ethylamidosuccinimido)-3-aminopropyl)-N'-methyl-1,3-propanediamine in a minimal amount of methanol was treated with a solution of 407.1 mg (2.12 mmole) citric acid dissolved in a minimal amount of methanol at room temperature. After stirring for 5 min the volatiles where removed in vacuo to give 1.4027 g of the desired product as a red solid.

Workup

  1. customremoved in vacuo

Sources & evidence

ORD record
ord-d43c641aa6fe4a19bd7d3afd3ed44ec0
Source dataset
uspto-grants-1998_12
Patent number
US05854409

Reaction notes

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